Potassium Carbonate → HCID 59427899, compound

Participants

Reaction Steps

A solution of 1-allyl-4-methylpiperazine (2.12 g, 14.0 mmol) and 9-BBN (0.5 M in THF, 1.7 g, 28 mL, 14.0 mmol) was heated at reflux for 3 h and then cooled to RT. The solution was added to a mixture of 3-bromo-5-(trifluoromethyl)aniline (3.0 o g, 12.5 mmol), potassium carbonate (8.64 g, 62.5 mmol), PdCl2(PPh3)2-CH2Cl2 adduct (0.457 g, 0.6 mmol), DMF (30 mL) and water(2 mL). The mixture was heated to 75° C. for 24. The mixture was concentrated, triturated with dichloromethane, and filtered. The filtrate was concentrated and the residue was purified via column chromatography on silica gel (gradient elution with 0-20% methanol-dichloromethane) to afford 3-(3-(4-methylpiperazin-1-yl)propyl)-5-(trifluoromethyl)benzenamine as a brown oil. MS m/z=302 [M+H]+. Calc'd for C15H22F3N3: 301.

Provenance & Evidence